CN106008657B - Ku Zhi bitter principles I and extracting method and purposes - Google Patents
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- CN106008657B CN106008657B CN201610341691.0A CN201610341691A CN106008657B CN 106008657 B CN106008657 B CN 106008657B CN 201610341691 A CN201610341691 A CN 201610341691A CN 106008657 B CN106008657 B CN 106008657B
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- DFGSQFCZTGNHMC-UHFFFAOYSA-N C[N+](C1C2)(C1C2C1CC1)C(C1)C23C1=C2C3 Chemical compound C[N+](C1C2)(C1C2C1CC1)C(C1)C23C1=C2C3 DFGSQFCZTGNHMC-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/81—Solanaceae (Potato family), e.g. tobacco, nightshade, tomato, belladonna, capsicum or jimsonweed
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Abstract
It is the structure for having formula (I) the invention discloses Ku Zhi bitter principles I and extracting method and purposes , Ku Zhi bitter principles I：
Description
Technical field
The present invention relates to field of traditional Chinese medicine extraction, is related to Ku Zhi bitter principles I and extracting method and purposes.
Background technology
Bitter Zhi (Physalis angulata L.), also known as Chinese lantern, little groundcherry herb or fruit, Herba seu Fructus Physalis Minimae, Piao Piaocao, beat volume bubble etc.,
For Solanaceae (Solanaceae) Physalis (Physalis) annual herb plant.《Luchuan book on Chinese herbal medicine》With《Chinese book on Chinese herbal medicine》Dui Ku Zhi
Medicinal efficacy have detailed record, bitter Zhi has promoting the circulation of qi, dissipate-swelling, diuresis, controls abdominal distension, clearing heat and detoxicating, diuresis hemostasis, detumescence
Dissipating bind, available for treating abscess of throat, lung carbuncle, parotitis；The diseases such as difficult urination, blood urine swelling and aching of gum, pemphigus.It is among the people more
For treating the diseases such as blister sore, swelling and aching of gum, jaundice with damp-heat pathogen, red swelling and pain of throat, cough with lung heat.Domestic and foreign scholars pass through body
Interior, experiment in vitro confirms Ku Zhi anti-inflammatory (Choi, E.M.；et al.Investigations of anti-
inflammatory and antinociceptive activities of Piper cubeba,Physalis angulata
And Rosa hybrida.Journal of Ethnopharmacology 2003,89,171-175.), antitumor (He, H.；
et al.Physalin A induces apoptotic cell death and protective autophagy in
HT1080human fibrosarcoma cells.Journal of Natural Products,2013,76,880–888.)、
Antibacterial (Silva, M.T.G.；et al.Studies on antimicrobial activity,in vitro,of
Physalis angulata L.(Solanaceae)fraction and physalin B bringing out the
importance of assay determination.Memorias do Instituto Oswaldo Cruz 2005,
100,779-782.), anti-oxidant (Choi, E.M.；et al.Effect of some medicinal plants on
plasma antioxidant system and lipid levels in rats.Phytotherapy
The effect such as research.2005,19,382-386.).
But Ku Zhi bitter principle I, extracting method are extracted in Cong Ku Zhi, and there is not been reported for purposes.
The content of the invention
It is an object of the invention to provide Ku Zhi bitter principles I.
Second object of the present invention is to provide Ku Zhi bitter principles I extracting method.
Third object of the present invention is to provide Ku Zhi bitter principles I purposes.
Fourth object of the present invention is to provide the Ku Zhi bitter principles I Ku Zhi extracts comprising claim 1.
The 5th purpose of the present invention is to provide the purposes of Ku Zhi extracts.
The 6th purpose of the present invention is to provide Han Ku Zhi bitter principles I pharmaceutical composition.
The 7th purpose of the present invention is to provide the purposes of aforementioned pharmaceutical compositions.
Technical scheme is summarized as follows：
Ku Zhi bitter principle I, there is the structure of formula (I)：
Ku Zhi bitter principles I extracting method, comprises the following steps：
(for 1) using Ku Zhi drying cauline leaf as raw material, the volume fraction for adding raw material 8-10 mass times is 60%-80% ethanol
The aqueous solution, refluxing extraction 2-3 times, extract every time 2-3 hours, merging obtains extract solution, and solvent is recovered under reduced pressure, and is obtained after concentration total
Medicinal extract；
(2) total medicinal extract is distributed in the water of 5-10 mass times, extracted successively with petroleum ether and ethyl acetate, acetic acid
Solvent is recovered under reduced pressure in ethyl ester extract, obtains ethyl acetate layer medicinal extract；
(3) ethyl acetate layer medicinal extract separates through silica gel column chromatography, is respectively 100 with volume ratio:1、50:1 and 30:The two of 1
Chloromethanes-methanol elutes for eluent gradient, obtains cut Fr.1, Fr.2, Fr.3；
(4) cut Fr.3 separates through silica gel column chromatography, is respectively 10 with volume ratio:1、8:1 and 6:1 petroleum ether-acetone
Eluted for eluent gradient, obtain cut Fr.3-1, Fr.3-2, Fr.3-3；
(5) cut Fr.3-3 is through Sephadex LH-20 pillar layer separations, using volume ratio as 1:1 methylene chloride-methanol
For eluant, eluent isocratic elution, cut Fr.3-3-1 and Fr.3-3-2 are obtained；
(6) cut Fr.3-3-2 is through ODS pillar layer separations, using volume ratio as 1:9、3:7、5:5 and 8:2 methanol-water is
Eluent gradient elutes, and obtains cut Fr.3-3-2-1, Fr.3-3-2-2, Fr.3-3-2-3 and Fr.3-3-2-4；
(7) cut Fr.3-3-2-4 separates through silica gel preparative thin layer chromatography, using volume ratio as 1:1 dichloromethane-acetone
Prepared for solvent, obtain cut Fr.3-3-2-4-1；
(8) cut Fr.3-3-2-4-1 is through preparing HPLC chromatogram, using volume ratio as 1:1 methanol-water is mobile phase, is carried out
Purifying, obtains the bitter principles of Ku Zhi shown in Formulas I I.
Ku Zhi bitter principles I are preparing antineoplastic and are preparing the application in suppressing cell release NO medicines.
Include Ku Zhi bitter principle I Ku Zhi extracts.
Ku Zhi extracts are preparing antineoplastic and are preparing the application in suppressing cell release NO medicines.
A kind of pharmaceutical composition, include Ku Zhi bitter principles I or its pharmaceutically acceptable salt, and pharmaceutically acceptable carrier
And/or excipient.
Aforementioned pharmaceutical compositions are preparing antineoplastic and are preparing the application in suppressing cell release NO medicines.
Advantages of the present invention：
Ku Zhi bitter principles I of the present invention can effectively suppress nitric oxide (NO) release, prompt the compounds of this invention to make
For the medicine of anti-inflammatory.Ku Zhi bitter principles I can effectively suppress tumor promotion.
Embodiment
Technical scheme is described below in conjunction with specific embodiment, described embodiment is only this
Invention part of the embodiment, rather than whole embodiments.Based on the embodiment in the present invention, those of ordinary skill in the art exist
The every other embodiment obtained under the premise of creative work is not made, belongs to the scope of protection of the invention.
Embodiment 1
Ku Zhi bitter principles I extracting method, comprises the following steps：
(1) Yi Ku Zhi (Physalis angulata L.) drying cauline leaf (9.5kg) is raw material, adds the mass of raw material 9
Volume fraction again is 75% ethanol water, and refluxing extraction 2 times, extraction 2 hours, merge and obtain extract solution, depressurize back every time
Solvent is received, total medicinal extract (1370g) is obtained after concentration；
(2) total medicinal extract is distributed in the water of 5 mass times, extracted successively with isometric petroleum ether and ethyl acetate,
Solvent is recovered under reduced pressure in acetic acid ethyl acetate extract, obtains ethyl acetate layer medicinal extract 116g；
(3) ethyl acetate layer medicinal extract separates through silica gel column chromatography, is respectively 100 with volume ratio:1、50:1 and 30:The two of 1
Chloromethanes-methanol elutes for eluent gradient, obtains cut Fr.1, Fr.2, Fr.3 (35g)；
(4) cut Fr.3 separates through silica gel column chromatography, is respectively 10 with volume ratio:1、8:1 and 6:1 petroleum ether-acetone
Eluted for eluent gradient, obtain cut Fr.3-1, Fr.3-2, Fr.3-3 (4.2g)；
(5) cut Fr.3-3 is through Sephadex LH-20 pillar layer separations, using volume ratio as 1:1 methylene chloride-methanol
For eluant, eluent isocratic elution, cut Fr.3-3-1 and Fr.3-3-2 (600mg) are obtained；
(6) cut Fr.3-3-2 is through ODS pillar layer separations, using volume ratio as 1:9、3:7、5:5 and 8:2 methanol-water is
Eluent gradient elutes, and obtains cut Fr.3-3-2-1, Fr.3-3-2-2, Fr.3-3-2-3 and Fr.3-3-2-4 (500mg)；
(7) cut Fr.3-3-2-4 separates through silica gel preparative thin layer chromatography, using volume ratio as 1:1 dichloromethane-acetone
Prepared for solvent, obtain cut Fr.3-3-2-4-1；
(8) cut Fr.3-3-2-4-1 is through preparing HPLC chromatogram, using volume ratio as 1:1 methanol-water is mobile phase, is carried out
Purifying, obtains compound I (17mg).
The physical chemistry and constant of compound 1 are as follows：
Compound 1：Unformed powder；(c 0.1, MeOH)；UV(MeOH)λmax(log ε) 208 (1.4),
220(4.0)nm；IR(KBr)νmax3395,2921,2850,1740,1712,1647,1467,1382,1228,1134cm-1；CD
(MeOH) nm (Δ ε) 247 (+5.9), 294 (- 1.1)；HRESIME m/z 581.2726[M+Na]+(calcd for
C31H42O9Na, 581.2727), the molecular formula for determining compound 1 is C31H42O9；1H (400MHz, pyridine-d5) and13C-NMR
(100MHz, pyridine-d5) tables of data 1.
The carbon spectrum and hydrogen modal data of the compound 1 of table 1
Note：1H-NMR, 400MHz, pyridine-d5；13C-NMR, 100MHz, pyridine-d5。
Section (MS and NMR) is learned to do by physicochemical constant and Modern spectroscopy, with reference to document related data, identifies its structure,
Compound 1 is to have no the noval chemical compound of document report, as follows：
Embodiment 2
Ku Zhi bitter principles I extracting method, comprises the following steps：
(for 1) using Ku Zhi drying cauline leaf as raw material, the volume fraction for adding the mass times of raw material 8 is 80% ethanol water,
Refluxing extraction 3 times, every time extraction 2 hours, merging obtain extract solution, solvent are recovered under reduced pressure, total medicinal extract is obtained after concentration；
(2) total medicinal extract is distributed in the water of 5 mass times, extracted successively with isometric petroleum ether and ethyl acetate,
Solvent is recovered under reduced pressure in acetic acid ethyl acetate extract, obtains ethyl acetate layer medicinal extract；
(3)-(8) are the same as embodiment 1 (3)-(8).
Embodiment 3
Ku Zhi bitter principles I extracting method, comprises the following steps：
(for 1) using Ku Zhi drying cauline leaf as raw material, the volume fraction for adding the mass times of raw material 10 is 60% ethanol water,
Refluxing extraction 3 times, every time extraction 2 hours, merging obtain extract solution, solvent are recovered under reduced pressure, total medicinal extract is obtained after concentration；
(2) total medicinal extract is distributed in the water of 10 mass times, extracted successively with isometric petroleum ether and ethyl acetate,
Solvent is recovered under reduced pressure in acetic acid ethyl acetate extract, obtains ethyl acetate layer medicinal extract；
(3)-(8) are the same as embodiment 1 (3)-(8).
Embodiment 4
Ku Zhi bitter principle I antitumor activities detect
Using MTT methods, Dui Ku Zhi bitter principles I carries out Activity determination, with Human Prostate Cancer Cells (C4-2B and 22Rvl), people
Kidney cancer cell (786-O, A-498 and ACHN), exemplified by human melanoma cell (A375-S2).Above-mentioned cell purchase in
ATCC (USA, phone：800-638-6597, time buying in September, 2014)
The μ L of above-mentioned cell 100 in exponential phase are taken, per hole 2 × 104It is inoculated in 96 orifice plates, puts CO2Incubator
(37 DEG C, 5%CO2, saturated humidity) and culture.
Dosing (Ku Zhi bitter principle I after 12 hours) 10 μ L/ holes, the working solution of sample is used inactivates (56 DEG C, 30min) containing 10% heat
Hyclone (Gibco, USA), 100U/mL Benzylpenicillin sodium salts (Gibco, USA), 100 μ g/mL streptomysins (Gibco, USA)
It is respectively 10,5,2.5,1.25 that RPMI 1640 (Gibco, USA) or EMEM (Gibco, USA) liquid medium, which are diluted to final concentration,
0.625,0.3125,0.15625 μM, sample-adding group and blank group are all provided with 3 multiple holes.After continuing culture 72 hours, MTT work is added
Liquid, 20 μ L/ holes, after 3 hours, culture medium is discarded, adds the μ L/ holes of DMSO 150,500rpm is shaked 3 minutes on plate shaker, is used
ELIASA determines the OD values in each hole, and measure wavelength is 490nm, calculates cell proliferation inhibition rate, cell proliferation inhibition rate=(blank
Control group OD values-administration group OD values)/blank control group OD value × 100%.Test above in triplicate, Activity Results (IC50)
It is shown in Table 2.
The Ku Zhi bitter principles I of table 2 antitumor activity result (IC50,μM)
Embodiment 5
Ku Zhi bitter principles I suppresses the active testing that mouse macrophage RAW 264.7 discharges nitric oxide (NO)
Mouse macrophage RAW 264.7 (ATCC) is incubated at containing 10% heat inactivation (56 DEG C, 30min) hyclone
(Gibco), RPMI 1640 (Gibco) nutrient solution of 100U/mL Benzylpenicillin sodium salts (Gibco), 100 μ g/mL streptomysins (Gibco)
In, 37 DEG C, 5%CO2Constant incubator in be incubated growth.Because NO is extremely unstable, generation quickly in cell culture supernatant
Thank into nitrito- (NO2 -), therefore use NO in Griess method determination samples2 -The concentration index horizontal as NO is weighed.
Griess reagent As：0.1%N- naphthodiamides hydrochloride (naphthylethylenediaminedihydrochloride) is dissolved in
In water；Griess reagents B：1% P-aminobenzene-sulfonamide (sulphanilamide) is dissolved in 5%H3PO4In.Using preceding isometric
Mix reagent A and B.The cells of RAW 264.7 are diluted to 5 × 10 with RPMI 1640 culture mediums5Cells/mL concentration, is inoculated in
In 96 porocyte culture plates, 200100 μ L cell suspending liquids are added per hole.CO2After cultivating 1h in incubator, it is more that fat is added per hole
Sugared (lipopolysaccharide, LPS) (Sigma) (the μ g/mL of final concentration 1) and the various concentrations of DMSO dissolvings test sample
0%) and blank control group 0.4 μ L, while set LPS groups and (add LPS, but be added without test sample, to the inhibiting rates of NO releases for
(LPS and test sample are added without, only adds 0.4 μ L DMSO, the inhibiting rate to NO releases is that 100%) each sample sets 4
Parallel hole.At 37 DEG C, 5%CO2Constant incubator in cultivate 24h, draw 100 μ L nutrient solution supernatants into ELISA Plate, centrifugation
(1000 × g, 4 DEG C, 3min), 100 μ L Griess reagents are added, room temperature lucifuge reaction 10min, its 540nm are determined in ELIASA
Locate light absorption value.It is respectively 1,5,10,50 μm of ol/L NaNO with concentration2Standard curve is drawn, according to NaNO2Standard curve cell
NO in culture supernatant2 -Concentration so that calculate the inhibiting rate that is discharged to NO of test sample.
The suppression NO releasing results of the compound of table 3
The anti-inflammatory drug of composition containing compound of the present invention can be to apply shape suitable for oral or injection etc.
Formula, for example, routinely technology, adds pharmaceutically acceptable carrier and/or excipient and tablet, capsule, pulvis, syrup is made
Agent, injection etc..
Compound has pharmacological activity, and therefore, the composition containing the compound also has pharmacological activity.
The explanation of above example is only intended to help the method and its central idea for understanding the present invention.It should be pointed out that pair
For one of ordinary skill in the art, under the premise without departing from the principles of the invention, the present invention can also be carried out some
Improve and modify, these are improved and modification also falls into the protection of the claims in the present invention.
Ku Zhi bitter principles I of the present invention, Han Ku Zhi bitter principles I extract, Han Ku Zhi bitter principles I composition can prepare treatment one
The medicine of nitric oxide metabolism exception associated diseases.
Its associated disease includes：Systemic inflammatory response syndrome, hypertension, cerebral thrombus, heart failure, hepatic sclerosis,
Rheumatoid arthritis, osteoarthritis, joint of vertebral column inflammation, inflammatory bowel disease, acute pancreatitis, peritonitis, cholecystitis, appendicitis,
Diabetes, systemic loupus erythematosus, dermatitis flesh, psoriasis, acute myeloid leukaemia, parkinsonism, alzheimer's disease, depression
Disease, septicemia, chronic obstructive pneumonia, asthma, acute pancreatitis, central nervous system injury etc..Secondly, NO metabolic disorders also with cancer
Become and the hyperplasia of cancerous tissue be relevant, the NO of high concentration also can modificator gene mutation and tumour, above-claimed cpd, which can suppress NO, to be released
Put, so as to play antineoplastic action.Applicable tumour example includes but is not limited to：Various entity tumors and leukaemia, such as lung
Cancer, liver cancer, cancer of pancreas, stomach cancer, osteocarcinoma, cancer of the esophagus, prostate cancer, colon cancer, oophoroma, carcinoma of urinary bladder, cervix cancer, melanin
Knurl, carcinoma of testis, bronchiolar carcinoma, clear-cell carcinoma, cholangiocarcinoma, choriocarcinoma, spongiocytoma, neurofibroma, fibrosarcoma, leaching
Hand shaft knurl etc..
Claims (7)
1. Ku Zhi bitter principle I, it is characterized in that the structure with formula (I)：
2. Ku Zhi bitter principles I extracting method described in claim 1, it is characterised in that comprise the following steps：
(1) using bitter Zhi drying cauline leaf as raw material, the volume fraction for adding raw material 8-10 mass times is water-soluble for 60%-80% ethanol
Liquid, refluxing extraction 2-3 times, extract every time 2-3 hours, merging obtains extract solution, and solvent is recovered under reduced pressure, is always soaked after concentration
Cream；
(2) total medicinal extract is distributed in the water of 5-10 mass times, extracted successively with petroleum ether and ethyl acetate, ethyl acetate
Solvent is recovered under reduced pressure in extract, obtains ethyl acetate layer medicinal extract；
(3) ethyl acetate layer medicinal extract separates through silica gel column chromatography, is respectively 100 with volume ratio:1、50:1 and 30:1 dichloromethane
Alkane-methanol elutes for eluent gradient, obtains cut Fr.1, Fr.2, Fr.3；
(4) cut Fr.3 separates through silica gel column chromatography, is respectively 10 with volume ratio:1、8:1 and 6:1 petroleum ether-acetone is to wash
De- agent gradient elution, obtains cut Fr.3-1, Fr.3-2, Fr.3-3；
(5) cut Fr.3-3 is through Sephadex LH-20 pillar layer separations, using volume ratio as 1:1 methylene chloride-methanol is to wash
De- agent isocratic elution, obtains cut Fr.3-3-1 and Fr.3-3-2；
(6) cut Fr.3-3-2 is through ODS pillar layer separations, using volume ratio as 1:9、3:7、5:5 and 8:2 methanol-water is elution
Agent gradient elution, obtain cut Fr.3-3-2-1, Fr.3-3-2-2, Fr.3-3-2-3 and Fr.3-3-2-4；
(7) cut Fr.3-3-2-4 separates through silica gel preparative thin layer chromatography, using volume ratio as 1:1 dichloromethane-acetone is exhibition
Open agent to be prepared, obtain cut Fr.3-3-2-4-1；
(8) cut Fr.3-3-2-4-1 is through preparing HPLC chromatogram, using volume ratio as 1:1 methanol-water is mobile phase, is carried out pure
Change, obtain the bitter principles of Ku Zhi shown in Formulas I I.
3. claim 1 Ku Zhi bitter principles I are preparing antineoplastic and are preparing the application in suppressing cell release NO medicines.
4. include claim 1 Ku Zhi bitter principle I Ku Zhi extracts.
5. claim 4 Ku Zhi extracts answering in preparing antineoplastic and suppressing cell release NO medicines in preparation
With.
6. a kind of pharmaceutical composition, it is characterized in that Ku Zhi bitter principles I or its pharmaceutically acceptable salt comprising claim 1, and
Pharmaceutically acceptable carrier and/or excipient.
7. the pharmaceutical composition of claim 6 answering in preparing antineoplastic and suppressing cell release NO medicines in preparation
With.
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| WO2012106393A2 (en) * | 2011-02-01 | 2012-08-09 | University Of Kansas | Withanolide isolated from physalis longifolia and analogs and methods of use thereof |
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